50600-39-0

Basic information

• Product Name: 5-deoxy-5-iodo-1,2-O-(1-methylethylidene)pentofuranose
• CAS NO: 50600-39-0
• Molecular Formula: C₈H₁₃IO₄
• Molecular Weight: 300.0909
• Mol File: 50600-39-0.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 356.8°C at 760 mmHg
• Flash Point: 169.6°C
• Density: 1.751g/cm³
• Vapor Pressure: 1.59E-06mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: 5-deoxy-5-iodo-1,2-O-(1-methylethylidene)pentofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 5-deoxy-5-iodo-1,2-O-(1-methylethylidene)pentofuranose(50600-39-0)
• EPA Substance Registry System: 5-deoxy-5-iodo-1,2-O-(1-methylethylidene)pentofuranose(50600-39-0)

Safety Data

• Hazardous Substances Data: 50600-39-0(Hazardous Substances Data)

Upstream product

• 6893-65-8 1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose 
• 218621-71-7 6-hydroxy-2,2-dimethyl-5-(4-methylphenylsulfonyloxymethyl)-(3aS,5S,6R,6aS)-perhydrofuro[2,3-d][1,3]dioxole 
• 131156-47-3 (3aS,3bR,7aS,8aS)-2,2,5,5-tetramethyltetrahydro-3aH-[1,3]dioxolo[4',5':4,5]furo[3,2-d][1,3]dioxane 
• 114861-22-2 1,2-O-isopropylidene-α-L-xylofuranose 
• 609-06-3 L-xylose 
• 172657-97-5 1,2-O-isopropylidene-α-D-xylofuranose 3,5-O-thionocarbonate 
• 1189-71-5 isocyanate de chlorosulfonyle 
• 810667-99-3 propane-2-sulfonic acid 2,2-dimethyl-6-propenyloxy-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 

Downstream Products

• 132063-93-5 5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-xylo-oct-7-enofuranose 
• 4152-79-8 1,2-O-isopropylidene-5-methyl-5-deoxy-α-D-xylofuranose 
• 634-74-2 6-deoxy-D-gulose 
• 6422-34-0 D-gulomethylonic acid 
• 2079-46-1 D-xylo-6-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 13039-60-6 D-threo-5-deoxy-[2]pentosulose-bis-phenylhydrazone 
• 5531-26-0 D-threo-5-deoxy-[2]pentosulose-bis-(4-bromo-phenylhydrazone) 
• 16713-89-6 O¹,O²-isopropylidene-O³-(toluene-4-sulfonyl)-5-deoxy-α-D-xylofuranose 
• 20031-16-7 6-deoxy-D-gulono-1,4-lactone 
• 6422-34-0 L-gulomethylonic acid 
• 6422-34-0 L-idomethylonic acid 
• 69260-71-5 doxifluridine 
• 76462-82-3 1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil 
• 158112-55-1 5-O-deoxy-D-ribofuranose 

Relevant articles and documents

Dual course of bisacetonation of D-xylose in a system Me 2CO-Me2C(OMe)2-H2SO4

In the course of formation of a bisisopropylidene protective group by keeping D-xylose in a mixture Me2CO-(MeO)2CMe 2-H2SO4 alongside the expected 1,2:4,5-O-diisopropylidene derivative formed minor dimethylacetal, 2,3:4,5-O-diisopropylidene-D-xylose, inseparable from the main product by the chromatography on SiO2. The conditions were found for the selective formation and isolation of the latter, some its one-pot transformations were studied resulting in synthetically promising orthogonally protected acyclic C5-synthons.

Synthesis of nucleosides from 4-methylidenefuranoses: A non-classical electrophilic addition

The reaction of persilylated bases (thymine, uracil, cytosine, and 5-fluorouracil) with either 3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-α-D-erythro-pent-4-enofuranose 6 or its 3-O-benzyl analogue 7 in the presence of N-iodosuccinimide (NIS) afforded two types of product with high stereoselectivity; either (1′S,2′R,3′S)-3′-O-benzoyl- 8-10 or -3′-O-benzyl-5′-deoxy-5′-iodo-1′,2′-O- isopropylidene-4′-oxo-1′-yl-pyrimidines 11-13, respectively, from 1,4-addition with participation of the oxygen atom at the furanoid ring, and either 3′-O-benzoyl- 14-16, or 3′-O-benzyl-5′-deoxy-5′-iodo-1′,2′-O- isopropylidene-β-L-lyxo-4′-yl-pyrimidine and 17-19 resulting from normal electrophilic addition at the exocyclic methylene group. A third compound was isolated from the reaction of 7 with persilylated uracil/NIS and identified as the doubly N,N′-glycosylated pyrimidine 20.

Short Synthetic Route to Congeners of the Undecose Antibiotic Herbicidin

The undecose backbone of the herbicidins has been assemled via direct alkylation, hydroxyalkylation, or acylation of the cyclic vinylanion 5 with the xylofuranose triflate 14, aldehyde 6, or acid chloride 10, respectively.